Carbon Dioxide → 4-(Pentafluoro-lambda6-sulfanyl)benzoic acid
Reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13]([F:18])([F:17])([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[C:19](=[O:21])=[O:20].Cl>CCCCCC.CCOCC>[F:14][S:13]([F:18])([F:17])([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([C:19]([OH:21])=[O:20])=[CH:8][CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A solution of n-butyllithium (9.4 ml of a 1.6M solution in hexane) was added to a stirred solution of 4-bromophenylsulphur pentafluoride (3.87 g) in ether at -78° C. under an inert atmosphere. After maintaining at -78° C. for 1 hour, solid carbon dioxide (20 g) was added and the mixture allowed to warm to 5° C. during 1.5 hours. Hydrochloric acid (2M) was added, the mixture stirred for 0.5 hour and the organic phase separated and itself extracted with sodium carbonate solution. The basic extract was washed (ether) and acidified (hydrochloric acid). The precipitated solid was extracted (ether), dried (magnesium sulphate) and evaporated. The residue was triturated (hexane) to give 4-pentafluorosulphanylbenzoic acid as a fawn solid (1.2 g), m.p.188-190° C.
Workup
- temperatureto warm to 5° C. during 1.5 hours
- customthe organic phase separated
- extractionitself extracted with sodium carbonate solution
- extractionThe basic extract
- washwas washed (ether)
- extractionThe precipitated solid was extracted (ether)
- dry with materialdried (magnesium sulphate)
- customevaporated
- customThe residue was triturated (hexane)
Sources & evidence
- ORD record
- ord-66ca446703cd4b58a4e5fa51226ab989
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06013805
Reaction notes
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